An improved P(V)-N activation strategy for the synthesis of nucleoside diphosphate 6-deoxy-l-sugars
Four nucleoside diphosphate 6-deoxy-l-sugars have been efficiently synthesized by coupling sugar-1-phosphates prepared from the H-phosphonate precursors with nucleoside 5′-phosphoropiperidates in the presence of 4,5-dicyanoimidazole (DCI) as the activator. Compared to the conventional 1H-tetrazole-p...
Gespeichert in:
| Veröffentlicht in: | Tetrahedron 2014-01, Vol.70 (2), p.294-300 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 300 |
|---|---|
| container_issue | 2 |
| container_start_page | 294 |
| container_title | Tetrahedron |
| container_volume | 70 |
| creator | Sun, Qi Li, Xingjian Sun, Jian Gong, Shanshan Liu, Gang Liu, Guodong |
| description | Four nucleoside diphosphate 6-deoxy-l-sugars have been efficiently synthesized by coupling sugar-1-phosphates prepared from the H-phosphonate precursors with nucleoside 5′-phosphoropiperidates in the presence of 4,5-dicyanoimidazole (DCI) as the activator. Compared to the conventional 1H-tetrazole-promoted phosphoromorpholidate method, the new phosphoropiperidate/DCI system significantly shortened the reaction time and afforded nucleoside diphosphate sugars in excellent isolated yields.
[Display omitted] |
| doi_str_mv | 10.1016/j.tet.2013.11.059 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1744681480</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0040402013017614</els_id><sourcerecordid>1744681480</sourcerecordid><originalsourceid>FETCH-LOGICAL-c396t-a4a011fc746b5b5f8bfdbefd0b29668663845ac9adf22b60e7ae7338dfa15b053</originalsourceid><addsrcrecordid>eNp9kEFPGzEQha2KSg20P6A3H-HgxbPrdTbihBBQJNT20PZqee0xcbRZB48TNf8eo_Tc07u8bzTvY-wryAYk6OtNU7A0rYSuAWhkv_rAFqC0Er0CfcYWUioplGzlJ3ZOtJFSArTdgrnbmcftLqcDev7z8s-V-M6tK_FgS0wzp5JtwZcjDynzskZOx7kGReIp8HnvJkwUPXIfd-tEu3Vtcy08pr9HMQnav9hMn9nHYCfCL__ygv1-uP919008_3h8urt9Fq5b6SKssvWp4JZKj_3Yh2EMfsTg5diutB607gbVW7eyPrTtqCUuLS67bvDBQj_Kvrtgl6e7dc7rHqmYbSSH02RnTHsysFRKD6AGWatwqrqciDIGs8txa_PRgDTvQs3GVKHmXagBMFVoZW5ODNYNh4jZkIs4O_QxoyvGp_gf-g0xSn9M</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1744681480</pqid></control><display><type>article</type><title>An improved P(V)-N activation strategy for the synthesis of nucleoside diphosphate 6-deoxy-l-sugars</title><source>ScienceDirect Journals (5 years ago - present)</source><creator>Sun, Qi ; Li, Xingjian ; Sun, Jian ; Gong, Shanshan ; Liu, Gang ; Liu, Guodong</creator><creatorcontrib>Sun, Qi ; Li, Xingjian ; Sun, Jian ; Gong, Shanshan ; Liu, Gang ; Liu, Guodong</creatorcontrib><description>Four nucleoside diphosphate 6-deoxy-l-sugars have been efficiently synthesized by coupling sugar-1-phosphates prepared from the H-phosphonate precursors with nucleoside 5′-phosphoropiperidates in the presence of 4,5-dicyanoimidazole (DCI) as the activator. Compared to the conventional 1H-tetrazole-promoted phosphoromorpholidate method, the new phosphoropiperidate/DCI system significantly shortened the reaction time and afforded nucleoside diphosphate sugars in excellent isolated yields.
[Display omitted]</description><identifier>ISSN: 0040-4020</identifier><identifier>EISSN: 1464-5416</identifier><identifier>DOI: 10.1016/j.tet.2013.11.059</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>4,5-Dicyanoimidazole ; Activation ; Diphosphates ; H-Phosphonate ; Joining ; Nucleoside diphosphate sugar ; Nucleosides ; Phosphoropiperidate ; Precursors ; Strategy ; Sugar-1-phosphate ; Synthesis ; Tetrahedrons</subject><ispartof>Tetrahedron, 2014-01, Vol.70 (2), p.294-300</ispartof><rights>2013 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c396t-a4a011fc746b5b5f8bfdbefd0b29668663845ac9adf22b60e7ae7338dfa15b053</citedby><cites>FETCH-LOGICAL-c396t-a4a011fc746b5b5f8bfdbefd0b29668663845ac9adf22b60e7ae7338dfa15b053</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.tet.2013.11.059$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids></links><search><creatorcontrib>Sun, Qi</creatorcontrib><creatorcontrib>Li, Xingjian</creatorcontrib><creatorcontrib>Sun, Jian</creatorcontrib><creatorcontrib>Gong, Shanshan</creatorcontrib><creatorcontrib>Liu, Gang</creatorcontrib><creatorcontrib>Liu, Guodong</creatorcontrib><title>An improved P(V)-N activation strategy for the synthesis of nucleoside diphosphate 6-deoxy-l-sugars</title><title>Tetrahedron</title><description>Four nucleoside diphosphate 6-deoxy-l-sugars have been efficiently synthesized by coupling sugar-1-phosphates prepared from the H-phosphonate precursors with nucleoside 5′-phosphoropiperidates in the presence of 4,5-dicyanoimidazole (DCI) as the activator. Compared to the conventional 1H-tetrazole-promoted phosphoromorpholidate method, the new phosphoropiperidate/DCI system significantly shortened the reaction time and afforded nucleoside diphosphate sugars in excellent isolated yields.
[Display omitted]</description><subject>4,5-Dicyanoimidazole</subject><subject>Activation</subject><subject>Diphosphates</subject><subject>H-Phosphonate</subject><subject>Joining</subject><subject>Nucleoside diphosphate sugar</subject><subject>Nucleosides</subject><subject>Phosphoropiperidate</subject><subject>Precursors</subject><subject>Strategy</subject><subject>Sugar-1-phosphate</subject><subject>Synthesis</subject><subject>Tetrahedrons</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNp9kEFPGzEQha2KSg20P6A3H-HgxbPrdTbihBBQJNT20PZqee0xcbRZB48TNf8eo_Tc07u8bzTvY-wryAYk6OtNU7A0rYSuAWhkv_rAFqC0Er0CfcYWUioplGzlJ3ZOtJFSArTdgrnbmcftLqcDev7z8s-V-M6tK_FgS0wzp5JtwZcjDynzskZOx7kGReIp8HnvJkwUPXIfd-tEu3Vtcy08pr9HMQnav9hMn9nHYCfCL__ygv1-uP919008_3h8urt9Fq5b6SKssvWp4JZKj_3Yh2EMfsTg5diutB607gbVW7eyPrTtqCUuLS67bvDBQj_Kvrtgl6e7dc7rHqmYbSSH02RnTHsysFRKD6AGWatwqrqciDIGs8txa_PRgDTvQs3GVKHmXagBMFVoZW5ODNYNh4jZkIs4O_QxoyvGp_gf-g0xSn9M</recordid><startdate>20140114</startdate><enddate>20140114</enddate><creator>Sun, Qi</creator><creator>Li, Xingjian</creator><creator>Sun, Jian</creator><creator>Gong, Shanshan</creator><creator>Liu, Gang</creator><creator>Liu, Guodong</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20140114</creationdate><title>An improved P(V)-N activation strategy for the synthesis of nucleoside diphosphate 6-deoxy-l-sugars</title><author>Sun, Qi ; Li, Xingjian ; Sun, Jian ; Gong, Shanshan ; Liu, Gang ; Liu, Guodong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c396t-a4a011fc746b5b5f8bfdbefd0b29668663845ac9adf22b60e7ae7338dfa15b053</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>4,5-Dicyanoimidazole</topic><topic>Activation</topic><topic>Diphosphates</topic><topic>H-Phosphonate</topic><topic>Joining</topic><topic>Nucleoside diphosphate sugar</topic><topic>Nucleosides</topic><topic>Phosphoropiperidate</topic><topic>Precursors</topic><topic>Strategy</topic><topic>Sugar-1-phosphate</topic><topic>Synthesis</topic><topic>Tetrahedrons</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sun, Qi</creatorcontrib><creatorcontrib>Li, Xingjian</creatorcontrib><creatorcontrib>Sun, Jian</creatorcontrib><creatorcontrib>Gong, Shanshan</creatorcontrib><creatorcontrib>Liu, Gang</creatorcontrib><creatorcontrib>Liu, Guodong</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sun, Qi</au><au>Li, Xingjian</au><au>Sun, Jian</au><au>Gong, Shanshan</au><au>Liu, Gang</au><au>Liu, Guodong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An improved P(V)-N activation strategy for the synthesis of nucleoside diphosphate 6-deoxy-l-sugars</atitle><jtitle>Tetrahedron</jtitle><date>2014-01-14</date><risdate>2014</risdate><volume>70</volume><issue>2</issue><spage>294</spage><epage>300</epage><pages>294-300</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><abstract>Four nucleoside diphosphate 6-deoxy-l-sugars have been efficiently synthesized by coupling sugar-1-phosphates prepared from the H-phosphonate precursors with nucleoside 5′-phosphoropiperidates in the presence of 4,5-dicyanoimidazole (DCI) as the activator. Compared to the conventional 1H-tetrazole-promoted phosphoromorpholidate method, the new phosphoropiperidate/DCI system significantly shortened the reaction time and afforded nucleoside diphosphate sugars in excellent isolated yields.
[Display omitted]</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.tet.2013.11.059</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0040-4020 |
| ispartof | Tetrahedron, 2014-01, Vol.70 (2), p.294-300 |
| issn | 0040-4020 1464-5416 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1744681480 |
| source | ScienceDirect Journals (5 years ago - present) |
| subjects | 4,5-Dicyanoimidazole Activation Diphosphates H-Phosphonate Joining Nucleoside diphosphate sugar Nucleosides Phosphoropiperidate Precursors Strategy Sugar-1-phosphate Synthesis Tetrahedrons |
| title | An improved P(V)-N activation strategy for the synthesis of nucleoside diphosphate 6-deoxy-l-sugars |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-07T00%3A08%3A17IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=An%20improved%20P(V)-N%20activation%20strategy%20for%20the%20synthesis%20of%20nucleoside%20diphosphate%206-deoxy-l-sugars&rft.jtitle=Tetrahedron&rft.au=Sun,%20Qi&rft.date=2014-01-14&rft.volume=70&rft.issue=2&rft.spage=294&rft.epage=300&rft.pages=294-300&rft.issn=0040-4020&rft.eissn=1464-5416&rft_id=info:doi/10.1016/j.tet.2013.11.059&rft_dat=%3Cproquest_cross%3E1744681480%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1744681480&rft_id=info:pmid/&rft_els_id=S0040402013017614&rfr_iscdi=true |